Welcome to the New Normal: Escaping the 9-to-5 for Good

Kristin Wilson
Oct 8, 2018 · 8 min read

How I went from grad school to digital nomad and never looked back.

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Photo by rawpixel on Unsplash


  • Saying goodbye to meetings and corporate dress codes.
  • Waking up naturally — every day.
  • Going to workout classes without waiting lists.
  • Eliminating your daily commute. (Rush hour? What’s that?)
  • Taking your lunch break — or a vacation — whenever you choose.
  • Not having to answer to a boss. Or to anyone.
  • Declaring when your weekend starts and ends.
  • Being able to travel around the world at whim.

This is the reality for an increasing number of people who have traded the toxic 9-to-5 grind for the sovereignty and freedom of the laptop lifestyle. And it’s a reality that’s well within reach for workers in 2018 and beyond.

Look — there’s a high likelihood that you’ve already realized you don’t need to sit in your office to get your work done. There’s another way — one that involves leaving the rat race behind for good.

Life as a digital nomad sort of feels like living during the apocalypse, but in a good way. While most people are stuck in their cubicles, you can enjoy uncrowded streets and open tables at your favorite restaurants. If you bring your laptop along, that table can also double as a pretty good desk.

It feels like you’re cheating the system — because you are.

No one told you this was possible.

No textbook, no politician, no professor, no career counselor… NO ONE.

No one said you could live life on your own terms, doing whatever you wanted to earn a paycheck — especially without ever having to set foot in an office. Yet, that’s what I’ve done throughout my entire career.

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Costa Rica 2006

How It All Began for Me

My life started out as vanilla as it comes: upper-middle-class America with a large, close-knit family. You know, the kind that goes out for breakfast together after church every Sunday.

I was a classic over-achiever growing up: competitive athlete, cheerleading captain, student council, homecoming court, summa cum laude sorority girl… You name it. My childhood resume read like a page from a college-prep guide. I was well on my way toward achieving the classic American dream. Until I wasn’t.

Just a couple months into my first semester of business school, I experienced severe burnout. It came in the form of a grand mal seizure on the floor of Atlanta Airport’s Terminal B. The white picket fence future I’d envisioned for myself collapsed in about two minutes. When you’re diagnosed with epilepsy at 21 years old, it feels like your sense of self gets revoked along with your driver’s license.

“If I was already having a major health crisis before starting my first real job,” I wondered, “what the hell would my mid-life crisis look like?”

I had no choice but to change course. I decided to move to Costa Rica and work in real estate instead of taking a position with a leading market research firm.

My professors, career placement advisors, and fellow cohorts alike where aghast: “You’ll ruin your resume,” they warned. In their eyes, I was throwing away an expensive education, a valuable job title, and a lot of potential.

Why work for pennies in a third world country when I could be climbing the corporate ladder?

Luckily, I ignored them, and discovered the extraordinary world of location independence. This was precisely two years before The Four-Hour Work Week hit bookshelves and hinted at what was to come.

A few months into my time living and working in Central America, I realized something that changed my outlook for good. My clients — the 60-something multimillionaire businessmen and retirees I had once aspired to emulate — had it all wrong.

On paper, they had “made it.” After all, these were people with 6–7 figures of disposable income to invest in beachfront real estate. But in reality, they were spending their life savings to mimic how I was living on a meager $1,000/month.

It was all backward.

But how could this be? They had done everything right — worked all their lives, saved money, got rich, retired on time. But here I was — 40 years younger — having way more fun on a shred of the income they had.

Something was either very right or very wrong.

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Happy Hour in Costa Rica, 2009

Choosing My Perspective

I decided I had it right. Your perception is your reality, after all. I had stumbled into a lifestyle that wasn’t supposed to be possible yet. I’d inadvertently hacked the system before #lifehacks were a thing. Burning out in grad school helped me find some sort of Golden Ticket.

I lived in a 2-story house with an ocean view, rode a 4x4 to work, and wore flip-flops all day. I went to yoga at sunrise and paddled out for a surf at sunset. Or vice versa.

Meanwhile, my former classmates back in the U.S. were working 80-hour weeks, with the lure of a promotion or a long weekend in Vegas keeping them going.

When my first year abroad was up, I assessed the situation.

Why the hell would I leave all this for a cubicle and a better job title?

So, I Stayed.

I fought the urge to cave to peer pressure, concerned parents, and societal expectations. I went down my own path that very few people understood at the time. And I’ve been abroad ever since.

It’s had its ups and downs. I enjoyed the real estate boom from Costa Rica then weathered the financial crisis from Nicaragua. I’ve traveled to over 55 countries and made thousands of friends. I retired from real estate in 2011 to launch my first online business venture, a relocation company for online poker players.

Life is pretty good. I’m still out here, doing my thing, writing this article from a hipster coffee shop in Amsterdam. It’s been 13 years to the month since I started on this journey.

I’m here to tell you all — a better way is possible. And the timing is right. The idea of being a professional globetrotter is now going mainstream.

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“Facebook in the Forest” — Photo by Kristin Wilson, Costa Rica, 2008

Why Digital Nomads, And Why Now?

You may be thinking, –“Thanks, Kristin! What the heck took you so long to say something?”

Well, hindsight is 20/20. Back in 2005, the Internet was still finding its feet. Facebook was only for college students, and the first generation iPhone was still two years away.

It also took me a while to determine with a high level of certainty that I had made the right decision out of college. It wasn’t my place to convince anyone that what I was doing was okay or that they should do it too. But I’m older and wiser now.

With today’s technology and remote work capabilities, there’s never been a better time for people to take chances. There’s no need to feel stuck or dread your future. The barriers to doing what you want in life have never been lower.

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Thoughtful waters — Photo by Luke Dahlgren on Unsplash

The #1 Lesson

The lesson I learned that first year in Costa Rica — one that kept resurfacing for me everywhere, from Berlin to Bali — is that you shouldn’t wait.

Don’t justify your current pain for a future outcome that’s not guaranteed. Don’t sacrifice yourself to placate others.

Even if you’re expected to take over the family business or become a doctor, remember that you only have one life. You don’t have to wait for a major health crisis or other wake-up call to remind you of that.

You don’t have to cave to the pressure and perceived expectations of others, either. In the unlikely case that your family or friends actually abandon you because you’re out following your dreams, so be it.

Far too many people stay within the confines of others’ expectations. It took my parents a good 8 years to stop asking me when I was moving back “home.” It took them almost as long to stop asking my brother when he would give up photography to go back to college.

My ex’s parents are probably still asking him to quit trading crypto and finish his engineering degree.

All three of us ignored our parents’ wishes, and we’re pretty damn happy.

I’m not saying you should follow our lead, but consider what’s the worst that could happen if you did what you wanted versus living for other people.

In his book, Willpower Doesn’t Work, Medium extraordinaire Benjamin P. Hardy says,

“The real decision [you need] to make is to cut off any relationships that contradict [your] goals.”

“Removing important people, such as friends and even family members, from your life can be very difficult. This doesn’t mean you must permanently banish them … the best thing you can do is be a good example for them. And you can’t be a good example by living below the level you believe you should.”

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Photo by Tyler Nix on Unsplash

What to Do Next

Look, guys — the proof is in the pudding. A location-independent lifestyle of freedom is viable. And it’s awesome. I can say that with certainty now.

So, here I am, spreading the word:

You don’t have to slave away at a job you hate.

Today, you can do almost any task from anywhere — whether you work for yourself or someone else. If I could do it with a 512kb satellite internet connection and Nokia cell phone in 2005, you can do it now.

Open your mind to the possibility and reality of a life without borders.

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Kristin Wilson

Written by

Content Creator: Host of Badass Digital Nomads Podcast and www.YouTube.com/TravelingwithKristin. Get my free remote jobs guide at: http://bit.ly/FreeJobsGuide

The Startup

Medium's largest active publication, followed by +754K people. Follow to join our community.

Kristin Wilson

Written by

Content Creator: Host of Badass Digital Nomads Podcast and www.YouTube.com/TravelingwithKristin. Get my free remote jobs guide at: http://bit.ly/FreeJobsGuide

The Startup

Medium's largest active publication, followed by +754K people. Follow to join our community.

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